Photographic developer and process of developing photographic materials



Patented Apr. 7, 1931 UNITED STATES PATENT, orFlce GUSTAV REDDELIEN ANDWERNER ntfiLLm-t,

NEW YORK or nnrrzro, GERMANY, ASSIGNORS ro AGFA. ANSCO CORPORATION, OFBINGHAMTON, NEW YORK, A CORPORATION OF PHOTOGRAPHIC DEVELOPER D PROCESSDEVELOPING PHOTOGRAPHIC MATERIALS No Drawing. Application filed October'1, 1928, Serial The present invention relates to new photographicdevelopers, more particularly to developers comprising as a developingagent a compound of the general formula wherein X represents asubstituent other than a nitro-group and at least one X is a substituentother than hydrogen, and to the proc-- 1o ess of developing photographicmaterials with these developers.

We found that photographic developers mide.N-mono-hydroxyethyl-derivatives ofnuclear substitution products orhomologues 25 of 4-amino-1-hydroxybenzene were hitherto unknown, themanufacture of them has been described in our co-pending applicationSerialNo. 309,887, filed October 2nd, 1928, and

, consists in the condensation of nuclear sub- 1 stitution products ofl-amino-l-hydrOxybenzene with a halogn-hydrin of glycol or with Suitablecompositions for photographic developers in accordance with the presentinvention are obtained by mix- 35 ing the developing agent with theordinary developer ingredients.-

Emample 1.-1.17 gram of the sulfate of ethyleneoxide.

4-hydroxyethyl amino-Q-chloro-l-hydroxy benzene,

9 grams of crystallized sodium sulflte and 5 grams or potassiumcarbonate are dissolved in 200 grams of water. j

This developer has all the valuable properties referredto in theforegoing.

Example 2.A developer of almost equal No. 303,687, and in GermanyN'ovember 21, 1927.

0 activity to that of the developer described in Example 1 is made bydissolvlng in 200 grams of water v 1 gram of the oxalate of4-hydroxyethy1amino-3-methyl-1- hydroxybenzene 3 grams of crystallizedsodium sulfite and 3 grams of potassium carbonate.

E wample 3.-Another developer, which is very similar in actlon to theknown l-amino- 1-hydroxybenzene-developer 1s made as follows: 1

Solution A: 3.65 grams. of 4-hydroxyethylamino-l-hydroxybenzene 2carboxylic acid and 5 grams of crystallized sodium sulfite are dissolvedin 200 grams of water.

10 grams of potassium hydroxide are dissolved in Solution B: 509 gramsof water.

For use, 1 part of. solution A, 1 part of solution B and 1 part of waterare mixed together.

We claim:

1. A photographic developer containing together with other developeringredients a compound of the general formula wherein at least one X isa substituent taking the place of a hydrogen atom, which substituent,however, should not be a nitro group. 2. A photographic developercontaining together with other developer ingredients a compound of thegeneraliformula wherein 3 Xs are hydrogen atoms and the 4th X is asubstituent other than a nitro group.

3. A photographicdeveloper containing together with otherdeveloperingredients a compound of the general formula wherein 3 Xs are hydrogenatoms and the 4th X is an alkyl roup.

4. A photograp ic developer containing 1 together with other developeringredients a compound of the general formula HO.C X .NH.CH .OH .9H,

methyl-1-hydroxybenzene.

6. A photographic developer containing together with sodium sulfite acompound of the. general formula HO.C X .NH.CH .CH .OH, wherein 3 Xs arehydrogen atoms and the 4th X is a substituent other than a nitro group.

. 7. A photographic developer containing together with sodium sulfite acompound of the general formula wherein 3 Xs are hydrogen atoms and the4th X is an alkyl roup.

8. A photograp ic developer containing together with sodium sulfite theoxalate of 4- hydroxyethylamino 3 methyl 1 hydroxybenzene.

9. A photographic developer 1 containing together with an alkalinesolution of sodium sulfite and potassium bromide, a compound of thegeneral formula Ho.c.x..NH.oH2.cH..o1-1,

wherein 3 Xs are hydrogen atoms and the 4th X is a substituent otherthan a nitro group.

10. A photographic developer containing together with an alkalinesolution of sodium sulfite and potassium bromide, the oxalate of 4hydroxyethylamino- 3-methyl-1-hydroxybenzene.

11. The process of developing photographic materials which comprisestreating the same with a solution containing a compound of the generalformula HOG X NHCH CH DH, wherein at least one X is a substituent takingthe place of a hydrogen atom, which subwherein 3 Xs are hydrogen atomsand the 4th X is a substituent other than a nitro group.

13. The process of developing photographic materials which comprisestreating the same with a solution containing a compound of the generalformula wherein 3 Xs are hydrogen atoms and the 4th X is an alkyl group.

14. The process of developing photographic materials which comprisestreating the same with a solution containing a compound of the generalformula wherein 3 Xs are hydrogent'atoms and the 4th X is a methylgroup.

15. The process of developing photographic materials which comprisestreating the same with a solution containing the 0xalate of4-hydroxyethylamino-3-methyl-lhydroxybenzene.

16. The process of developing photographic materials which comprisestreating the same with a solution containing together with otherdeveloper ingredients a compound of the general formulaHo.o.x..NH.oH..on..oH,

wherein 3 Xs are hydrogen atoms and the 4th X is. a substituent otherthan a nitro group.

17. The process of developing photographic materials which comprisestreating the same with a solution containing together with otherdeveloper ingredients the oxalate of 4 hydroxyethylamino 3 methyl- 1-hydroxybenzene.

18. The process of developing photographic materials which comprisestreating the same with a solution containing sodium sulfite and acompound of the general formula HO.C X .NH.CH .CH .OH, wherein 3 Xs arehydrogen atoms and the 4th X is a substituent other than a nitro group.

19. The process of developing photographic materials which comprisestreating the same with an alkaline solution of sodium sulfite and acompound of the general 20. The process of developing photo-- graphicmaterials which comprises treating the same with a solution containingsodium sulfite, potassium carbonate, and the oxalate of 4hydroxyethylamino 3 methyl- 1 -hydroxybenzene.

In testimony whereof, We afiix our signatures.

GUSTAV REDDELIEN.

WERNER MULLER.

